Naples, FL, United States

This self-proclaimed "Golf Capital of the World" is a magnet for retirees, with a median age of 61 and over 42% of the population aged 65 or older. The population sits at just 19,115, down from 19,539 a decade ago. While the pristine beaches and mild climate are appealing, the city is no stranger to hurricanes - 74 tropical storms have passed within 85 miles since 1851, including devastating hits from Wilma, Irma, and Ian. Bureaucracy is also a persistent headache, with the city only officially incorporating in 1949. Naples is best suited for affluent retirees seeking a quiet, golf-centric lifestyle along the Gulf Coast.